Sodium → 7-Bromo-1,2,3,4-tetrahydroisoquinoline

HRID 580930Notes

Reaction equation

HRID 580930 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1.[Na]>O>[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 232961917-Bromo-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinolineYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

219 g (0.89 mol) of 7-bromo-3,4-dihydro-isoquinoline hydrochloride and 1.5 liters of water were combined and heated to 50° C. 33.7 g (0.89 mol) of sodium borohydrde was added in portions over 0.5 hours at which time the temperature rose to 62° C. The reaction was then cooled to ambient temperature and extracted three times with 1 liter of dichloromethane. The combined organic layers were washed with 1 liter of saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to yield 173 g of an oil.

Workup

  1. customrose to 62° C
  2. temperatureThe reaction was then cooled to ambient temperature
  3. extractionextracted three times with 1 liter of dichloromethane
  4. washThe combined organic layers were washed with 1 liter of saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4d9854d7d7142adbda463bdbd2659ec
Source dataset
uspto-grants-1999_07
Patent number
US05919795

Reaction notes

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